Regarding to your concern, I think the previous feature was enhanced to a new feature where you could define a connection rule for USB device. Through the rule, Workstation knows which VM the USB needs to connect to. For details, Please refer to Connecting USB Devices to Virtual Machines

All behaviour is as expected (written in the Docs) on a Windows host with Windows VM environment except for the fact the autoconnection is not working. When a VM is started the USB device doesn't reconnect to the VM according to the rules set. It was working with version 14.

With this new feature, you can associate any USB device with a specific VM, regardless of which port the USB device is plugged into. The USB device will be connected to the associated VM when you plug the device into host port as long as the VM is powered on. But if the USB device is already connected to the host, when you power on the associated VM, the device will not automatically disconnect from host and connect to the VM.

I need the old behaviour back, because I have a USB dongle (that is a HID type and doesn't need additional drivers) that is always connected to the Physical Host machine and protects a software that I run only in guest VM environment. And when I start the guest VM without the USB dongle connected to it (guest) the software cannot run because the protection component (dongle) is missing.

Additionally I have two other Card reader devices with Digital certificates that I use only in the VM guest and I want them to connect automatically too. But I've observed that when I connect them to the host USB port there is no dialog box popping up to offer that I chose what to do next (connect it to host, guest ,etc). I can only manually connect it to the VM guest. And I see on the bottom bar that I can chose the Reader itself or Shared Reader device. There are two choices available.

If I chose Shared reader option, is the reader going to be available on the host and guest simultaneously. Although I don't need this.

USB HID device such as USB dongle or smart card, or keyboard/mouse will not use this ask_connect feature, because we don't want keyboard/mouse to be automatically connected to guest. For USB dongle or smart card reader, maybe we can give user a choice whether to enable this ask_connect feature.

2. You power on a VM. => At this step, you want your device to be automatically connected to the guest, correct?

Yes that is true, I don't think even if we enable ask_connect for USB dongle or smart card reader, it will work for you. It is because the feature only defines the behavior when user plugs in the USB device to host port, not when a VM is powered on. And I double previous autoconnect can achieve this. Both askconnect and autoconnect define the behavior when a USB device is plugged in.

and I want to point out to this link - Automatically connecting USB devices at virtual machine power on (1648) on VMware Knowledge Base

Just a quote from it

Details

This article provides steps to configure a particular USB device to automatically connect to a virtual machine while the virtual machine starts.

Solution

This article provides a workaround that lets you automatically connect a USB device if you do not have access to the host that runs the guest operating system, and therefore cannot manually connect the device using the VM > Removable Devices menu. For more information about the preferred way to connect USB devices through the menu, see Connecting USB Devices to Virtual Machine section in the Using VMware Workstation Guide.

For the smart card reader or dongle to be able to pop up dialog (i.e. to use ask_connect feature), you need to add below line to C:\ProgramData\VMware\VMware USB Arbitration Service\config.ini (if there is no such file, create it).

usb.quirks.device0 = “0xVID:0xPID allow”

You need to restart host for the change to take effect.

For the issue that when a VM is powered on, the USB device needs to be automatically connected to the VM, we filed an internal bug to track the issue. And the developer is working on it.

I just am trying out Workstation 15 and it is clear that it doesn't meet our requirements anymore.

I want to connect a USB device automatically to a virtual machine when starting the VM and can't since autoconnect setting in vmx doesn't work anymore. It doesn't even remember the connection status once manually connected if the VM is turned off!

Any update on when a fix might be coming? We are evaluating the product and it has gone far better than we anticipated, accept for the fact we can not route the attached Dictaphones to the correct VM client by default. While right clicking in the console and directing the mic to the right session might not seem like a lot, we are trying to make it so the Doctor does not even realize thier application is not running on the local host.